We are close to buying 50'-60- sailboat to live aboard and offer week-long charters on, in the Caribbean. Beyong our own advertising costs (website, etc.) what fees/taxes/costs are we looking at? In, say, the Grenadines or the BVI's? Anywhere else? Does each island charge a tax of any kind? We are grateful for any info here!

If your going legal I'd say you'd need to present your boat for inspection to the authorities in your area of operation, satisfy their requirements for safety/hygene/suitability and apply for the Operators Licence...As to fee's taxes.. they will vary... for example St Martin.. French side is different from Dutch side... Dutch side is dearer.. they want all the cash they can get..

__________________"You're not drunk if you can lie on the floor without holding on." Dean Martin"Life is far too important a thing ever to talk seriously about..." Oscar Wilde.. but boats.? then click on the link in the picture below..

So, what's your angle going to be? What are you going to offer that will make prospects choose you over the 1000 other privately chartered boats in the caribbean?

I only can speak for St. Martin, French Side, but they don't require much. The biggest expense is that the island governments want the tax on the revenue. So, you have to have a company and declare income. To be legal.

Your insurance will be about 40% more also. And all safety equipment MUST be inspected. Have you looked at sailonline.com. You can join an owners forum and get more specific info there.

A friend of mine that had stopped at Shelter Bay had a 50 cat and was going to Belize to do charters and diving and etc. When they were told about taxes and fees and etc around $30,000 they decided to forgo. Check out the costs first before you go overboard. You might be in for a big surprise

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So helpful to hear from you all! Thank you and would love more input ..

What if boat is registered in US (and we come back to Maine summers to charter also) .... can we just arrange pick up/drop off of charter customers (maybe one week per month) at some public dock in Caribbean during winters, and pay taxes to US? Do people do that?

So helpful to hear from you all! Thank you and would love more input ..

What if boat is registered in US (and we come back to Maine summers to charter also) .... can we just arrange pick up/drop off of charter customers (maybe one week per month) at some public dock in Caribbean during winters, and pay taxes to US? Do people do that?

Of course they do. We've pals who run and operate the charter business from outside the Caribbean, and pay taxes in the country of business operation. But they equally comply with whatever charter regulations apply in the countries through which they carry their guests.

You'll need a commercial Skippers license, commercial vessel licence/approval from home country that is recognised by your port/s of call... suitable insurance cover... and may be charged entry at a higher rate...Or you could sorta fly a shade under the radar... don't brag how well your doing locally...As long as monies/transactions stay in the States and any advertising is done only there you should be fine... as long as you meet the US taxes, insurance requirements etc...I would suggest though setting up a regular joining ceremony for the 'new crew' in a restaurant/bar that is locally owned to chuck some money into the local economy... and maybe a leaving one.... Someone I knew had a set up like that in Andratx, Mallorca in the 90's.. he did well as long as he was putting buisiness peoples way.. then after a year he figured he'd cut out the locals and put the extra's in his own pocket...The locals got together and decided he was taking the piss and had just used and dumped them...He woke one morning to find the Aduana's launch alongside and had a 'Denuncia' slapped on all but personal effects...a little goes a long way in some places... one does'nt bite the hand that feeds...

__________________"You're not drunk if you can lie on the floor without holding on." Dean Martin"Life is far too important a thing ever to talk seriously about..." Oscar Wilde.. but boats.? then click on the link in the picture below..

Well you could always make it tough for them by not showing your boats name in any pictures on the site... no www.blahblah.blah on the boom or other odds n sods.. any pic's re scenery islands other than the pick up drop off Isle...Just keep it general Islands Cruise's till the booking form/deposit stage...lol

__________________"You're not drunk if you can lie on the floor without holding on." Dean Martin"Life is far too important a thing ever to talk seriously about..." Oscar Wilde.. but boats.? then click on the link in the picture below..

Have you owned a boat this size before? I may be wrong, but a boat this size operating outside the US would require Documentation. The US Govt. asks all kinds of questions - including if you are planning to charter or not. Don't know about everyone else but Homeland Security knowing or not knowing what I'm up to makes me nervous. And once you have your OUPV or Masters, govt. also has your back. I would definitely go the "legal" route.
Also, the boat you talk of is quite roomy but my partner and I find it difficult to charter a boat that we're living on. We've tried and it dosen't seem to work. Privacy, personal stuff...of course, we only have one head.... :-)

But in response to OP, I would definately look to go legal - working under the radar can be surprisingly hardwork, and mostly works better if your business model doesn't need you to put head above parapet. and shout

Dealing with paperwork abroad can be a challenge, but that's mostly because starting from zero knowledge - but once mastered you then get to dob in any unlicensed business rivals Hey, it's business